3-Bromo-6-chloroimidazo(1,2-b)pyridazine → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

HRID 69212

Reaction equation

HRID 69212 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Mg])C.[F:15][C:16]1[C:25]([CH:26]=[O:27])=[C:24]([F:28])[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2>C1COCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([CH:26]([C:25]3[C:16]([F:15])=[C:17]4[C:22](=[CH:23][C:24]=3[F:28])[N:21]=[CH:20][CH:19]=[CH:18]4)[OH:27])=[CH:3][N:4]=2)[N:7]=1

Participants

5

Reactant 3

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 579172825,7-Difluoroquinoline-6-carbaldehyde2×HCID 178461629HCID 178461629, compound

Product 1

HCID 58147519(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (4.40 g, 18.95 mmol) was suspended in THF (189 mL) and the ethylmagnesium solution (3 M, 6.32 mL) was added slowly under nitrogen condition. The RM was stirred at rt for 15 min and the solution of 5,7-difluoro-quinoline-6-carbaldehyde (Intermediate F, 3.66 g, 18.95 mmol) was added. After 30 min, the reaction was quenched with 10% ammonium chloride. The precipitate was filtered off and a first part of the title compound was obtained as a white solid. The filtrate was concentrated and was taken up with 10% NH4Cl. The precipitate was filtered off and was washed with EtOAc. A second part of the title compound was obtained as a brown solid (tR 0.8 min (conditions 2), MH+=347).

Workup

  1. waitAfter 30 min
  2. customthe reaction was quenched with 10% ammonium chloride
  3. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-1835d5d588ce4b68a20bf0880f38cadb
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

Loading…